AR067397A1 - TRIAZOL DERIVATIVES WITH ANTI-BANERIGAN ACTIVITY - Google Patents

TRIAZOL DERIVATIVES WITH ANTI-BANERIGAN ACTIVITY

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Publication number
AR067397A1
AR067397A1 ARP080102852A ARP080102852A AR067397A1 AR 067397 A1 AR067397 A1 AR 067397A1 AR P080102852 A ARP080102852 A AR P080102852A AR P080102852 A ARP080102852 A AR P080102852A AR 067397 A1 AR067397 A1 AR 067397A1
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nrg
nrgc
group
nrere
nrcrc
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ARP080102852A
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Andreas Mantoulidis
Christian Klein
Irene Waizenegger
Steffen Steurer
Peter Ettmayer
Ioannis Sapountzis
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Boehringer Ingelheim Int
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Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
Publication of AR067397A1 publication Critical patent/AR067397A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Apropiados para el tratamiento de enfermedades que se caracterizan por una proliferacion celular excesiva o anormal, así como su uso para la preparacion de un medicamento con las propiedades previamente mencionadas. Reivindicacion 1: Compuestos caracterizados porque tienen la formula general (1) en donde R1 representa un heteroarilo de 5-10 miembros, eventualmente sustituido con uno o varios radicales iguales o diferentes, en cada caso, de modo independiente entre sí, seleccionados del grupo compuesto por Ra y Rb; R2 presenta la subestructura (2) o (3); R3 está seleccionado del grupo compuesto por hidrogeno, halogeno, -CN, -NO2, -NRRh, -ORh, -C(O)Rh, -C(O)NRhRh, -SRh, -S(O)Rh, -S(O)2Rh, alquilo C1-4, haloalquilo C1-4, cicloalquilo C3-7 y heterocicloalquilo de 3-7 miembros; R5 está seleccionado del grupo compuesto por alquilo C1-6, -Oalquilo C1-6, haloalquilo C1-6, -Ohaloalquilo C1-6, cicloalquilo C3-7, heterocicloalquilo de 3-7 miembros, todos los radicales previamente mencionados eventualmente sustituidos con alquilo C1, -CN u -OH; a) en presencia de la subestructura (2) uno de los radicales R6, R7 o R8 y b) en presencia de la subestructura (3) uno de los radicales R6 o R7 presenta una de las subestructuras (4) a (7) y en el caso a) los dos radicales restantes en cada caso de modo independiente entre sí y en el caso b) el segundo radical está/están seleccionados del grupo compuesto por hidrogeno, alquilo C1-6, -Oalquilo C1-6, -OH, -CN, -NHalquilo C1-6, -N(alquilo C1-6)2 y halogeno o c) en presencia de la subestructura (i) R5 representa un alquilo C1-6 o cicloalquilo C3-4 sustituido con un sustituyente -CN y R6, R7 y R8 representa en cada caso hidrogeno; R9 está seleccionado del grupo compuesto por hidrogeno y alquilo C1-6, R10 está seleccionado del grupo compuesto por Ra y -ORa, o el grupo -NR9R10 representa en general un heterocicloalquilo de 3-14 miembros con contenido de nitrogeno o heteroarilo de 5-12 miembros, eventualmente sustituido con uno o varios radicales iguales o diferentes seleccionados del grupo compuesto por Ra y Rb; R11, R12 y R13 equivalen en cada caso de modo independiente entre sí a un radical Ra, o R11 equivale a un radical Ra y el grupo NR12R13 representa junto un heterocicloalquilo de 3-14 miembros con contenido de nitrogeno, eventualmente sustituido con uno o varios radicales iguales o diferentes seleccionados del grupo compuesto por Ra y Rb, o R11 y R12 junto con los átomos a los que están unidos, forman un heterocicloalquilo de 4-14 miembros con contenido de nitrogeno, eventualmente sustituido con uno o varios radicales iguales o diferentes seleccionados del grupo compuesto por Ra y Rb, y R13 equivale a un radical Ra; R14, R15 y R16 en cada caso de modo independiente entre sí equivalen a un radical Ra, o R14 equivale a un radical Ra y el grupo NR15R16 representa junto un heterocicloalquilo de 3-14 miembros con contenido de nitrogeno, eventualmente sustituido con uno o varios radicales iguales o diferentes seleccionados del grupo compuesto por R y Rb, o R14 y R15 junto con los átomos a los que están unidos, forman un heterocicloalquilo de 4-14 miembros con contenido de nitrogeno, eventualmente sustituido con uno o varios radicales iguales o diferentes seleccionados del grupo compuesto por Ra y Rb, y R16 equivale a un radical Ra; R17, R18 y R19 en cada caso de modo independiente entre sí equivalen a un radical Ra, o R17 y R18 junto con los átomos a los que están unidos, forman un heterocicloalquilo de 3-14 miembros con contenido de nitrogeno, eventualmente sustituido con uno o varios radicales iguales o diferentes seleccionados del grupo compuesto por Ra y Rb, y R19 equivale a un radical Ra; o R17 y R18 junto con los átomos a los que están unidos, forman un heterocicloalquilo de 414 miembros con contenido de nitrogeno, eventualmente sustituido con uno o varios radicales iguales o diferentes seleccionados del grupo compuesto por Ra y Rb, y equivale a un radical Ra; o R17 y R18 junto con los átomos a los que están unidos, forman un heterocicloalquilo de 414 miembros con contenido de nitrogeno, eventualmente sustituido con uno o varios radicales iguales o diferentes seleccionados del grupo compuesto por Ra y Rb, y R19 equivale a un radical Ra; L está seleccionado del grupo compuesto por -C(O)NH-, -NHC(O)-, -C(S)NH-, -NHC(S)-, -C(O)-, -C(S)-, -NH-, -S(O)-, -S(O)O-, -S(O)2-, -S(O)2O-, -S(O)NH-, -S(O)2NH-, -OS(O)-, -OS(O)2-, -OS(O)NH, -OS(O)2NH-, -C(O)O-, -C(O)S-, -C(NH)NH-, -OC(O)-, -OC(O)O-, -OC(O)NH-, -SC(O)-, -SC(O)O-, -SC(O)NH-, -NHC(NH)-, -NHS(O)-, -NHS(O)O-, -NHS(O)2-, -NHS(O)2O-, -NHS(O)2NH-, -NHC(O)O-, -NHC(O)NH- y -NHC(S)NH- o representa un enlace; Y está seleccionado del grupo compuesto por -O- y -S- o representa un enlace; x e y en cada caso de modo independiente entre sí tienen el valor 0, 1, 2 o 3; cada Ra es, en cada caso de modo independiente entre sí, hidrogeno o un radical sustituido eventualmente con uno o varios, iguales o diferentes Rb y/o Rc, seleccionado del grupo compuesto por alquilo C1-6, heteroalquilo de 2-6 miembros, halogenalquilo C1-6, cicloalquilo C3-10, cicloalquilalquilo C4-16, arilo C6-10, aril C7-16-alquilo, heteroarilo de 5-12 miembros, heteroarilalquilo de 6-18 miembros, heterocicloalquilo de 3-14 miembros y heterocicloalquilalquilo de 4-14 miembros; cada Rb es un sustituyente apropiado y en cada caso de modo independiente entre sí está seleccionado del grupo compuesto por -ORc, -SRc, -NRcRc, -ONRcRc, -N(ORc)Rc, -NRgNRcRc, halogeno, -CN, -NC, -OCN, -SCN, -NO, -NO2, -N3, -C(O)Rc, -C(O)ORc, -C(O)NRcRc, -C(O)SRc, -C(O)NRgNRcRc, -C(O)NRgORc, -[C(O)]2NRcRc, -[C(O)NRg]2Rc, -C(S)Rc, -C(S)ORc, -C(S)NRCRC, -C(S)SRc, -C(NRg)Rc, -N=CRcRc, -C(NR9)ORc, -C(NRg)NRc)Rc, -C(NRg)SRc, -C(NRg)NRgNRcRc, -C(NORg)Rc, -C(NORg)NRcRc, -C(NNRgRg)Rc, -C[NNRgC(O)NRgRg]Rc, -OS(O)Rc, -OS(O)ORc, -OS(O)NRcRc, -OS(O)2Rc, -OS(O)2ORc, -OS(O)2NRcRc, -OC(O)Rc, -OC(O)ORc, -OC(O)SRc, -OC(O)NRcRc, -O[C(O)]2NRcRc, -O[C(O)NRg]2NRcRc, -OC(S)Rc, -OC(NRg)Rc, -OC(NRg)NRcRc, -ONRgC(O)Rc, -S(O)Rc, -S(O)ORc, -S(O)NRcRc, -S(O)2Rc, -S(O)2ORc, -S(O)2NRcRc, -[S(O)2]2NRcRc, -SC(O)Rc, -SC(O)ORc, -SC(O)NRcRc, -SC(S)Rc, -SC(NRg)Rc, -SC(NRg)NRcRc, -NRgC(O)Rc, -NRgC(O)ORc, -NRgC(O)NRcRc, -NRgC(O)SRc, -NRgC(O)NRgNRcRc, -NRgC(S)Rc, -NRgC(S)NRcRc, -NRgC(NRg)Rc, -N=CRcNRcRc, -NRgC(NRg)ORc, -NRgC(NRg)NRcRc, -NRgC(NRg)SRc, -NRgC(NORg)Rc, -NRgS(O)Rc, -NRgS(O)ORc, -NRgS(O)2Rc, -NRgS(O)2ORc, -NRgS(O)2NRcRc, -NRgNRgC(O)Rc, -NRgNRgC(O)NRcRc, -NRgNRgC(NRg)Rc, -NRg[C(O)]2Rc, -NRg[C(O)]2ORc, -NRg[C(O)]2NRcRc, -[NRgC(O)]2Rc, -[NRgC(O)]2ORc, -NRg[S(O)2]2Rc, -N(ORg)C(O)Rc, -N[C(O)Rc]NRcRc, -N[C(O)Rc]2, -N[S(O)2Rc]2, -N{[C(O)]2Rc}2, -N{[C(O)]2ORc}2 y -N{[C(O)]2NRcRc}2 así como el sustituyente bivalente =O, =S, =NRg, =NORg, =NNRgRg y =NNRgC(O)NRgRg, en donde estos sustituyentes bivalentes solo pueden ser sustituyentes en sistemas de arillos no aromáticos; cada Rc es, de modo independiente entre si, hidrogeno o un radical sustituido eventualmente con uno o varios Rd y/o Re, iguales o diferentes, seleccionado del grupo compuesto por alquilo C1-6, heteroalquilo de 2-6 miembros, halogenalquilo C1-6, cicloalquilo C3-10, cicloalquilalquilo C4-16, arilo C6-10, arilalquilo C7-16, heteroarilo de 5-12 miembros, heteroarilalquilo de 6-18 miembros, heterocicloalquilo de 3-14 miembros y heterocicloalquilalquilo de 4-14 miembros; cada Rd es un sustituyente apropiado y en cada caso de modo independiente entre si está seleccionado del grupo compuesto por -ORe, -SRe, -NReRe, -ONReRe, -N(ORe)Re, -N(Rg)NReRe, halogeno, -CN, -NC, -OCN, -SCN, -NO, -NO2, -N3, -C(O)Re, -C(O)ORe, -C(O)NReRe, -C(O)SRe, -C(O)NRgNReRe, -C(O)NRgORe, -[C(O)]2NReRe, -[C(O)NRg]2Re, -C(S)Re, -C(S)ORe, -C(S)NReRe, -C(S)SRe, -C(NRg)Re, -N=CReRe, -C(NRg)ORe, -C(NRg)NReRe, -C(NRg)SRe, -C(NRg)NRgNReRe, -C(NORg)Re, -C(NORg)NReRe, -C(NNRgRg)Re, -C[NNRgC(O)NRgRg]Re, -OS(O)Re, -OS(O)ORe, -OS(O)NReRe, -OS(O)2Re, -OS(O)2ORe, -OS(O)2NReRe, -OC(O)Re, -OC(O)ORe, -OC(O)SRe, -OC(O)NReRe, -O[C(O)]2NReRe, -O[C(O)NRg]2NReRe, -OC(S)Re, -OC(NRg)Re, -OC(NRg)NReRe, -ONRgC(O)Re, -S(O)Re, -S(O)ORe, -S(O)NReRe, -S(O)2Re, -S(O)2ORe, -S(O)2NReRe, -[S(O)2]2NReRe, -SC(O)Re, -SC(O)ORe, -SC(O)NReRe, -SC(S)Re, -SC(NRg)Re, -SC(NRg)NReRe, -NRgC(O)Re, -NRgC(O)ORe, -NRgC(O)NReRe, -NRgC(O)SRe, -NRgC(O)NR9NReRe, -NRgC(S)Re, -NRgC(S)NReRe, -NRgC(NRg)Re, -N=CReNReRe, -NRgC(NRg)ORe, -NRgC(NRg)NReRe, -NRgC(NRg)SRe, -NRgC(NORg)Re, -NRgS(O)Re, -NRgS(O)ORe, -NRgS(O)2Re, -NRgS(O)2ORe, -NRgS(O)2NReRe, -NRgNRgC(O)Re, -NRgNRgC(O)NReRe, -NRgNRgC(NRg)Re, -NRg[C(O)]2Re, -NRg[C(O)]2ORe, -NRg[C(O)]2NReRe, -[NRgC(O)]2Re, [NRgC(O)]2ORe, -NRg[S(O)2]2Re, -N(ORg)C(O)Re, -N[C(O)Re]NReRe, -N[C(O)Re]2, -N[S(O)2Re]2, -N{[C(O)]2Re}2, -N{[C(O)]2ORe}2 y -N{[C(O)]2NReRe}2, así como el sustituyente bivalente =O, =S, =NRg, =NORg, =NNRgRg y =NNRgC(O)NRgRg, en donde estos sustituyentes bivalentes solo pueden ser sustituyentes en sistemas de anillos no aromáticos; cada Re es, de modo independiente entre si, hidrogeno o un radical sustituido eventualmente con uno o varios Rf y/o Rg iguales o diferentes, seleccionado del grupo compuesto por alquilo C1-6, heteroalquilo de 2-6 miembros, halogenalquilo C1-6, cicloalquilo C3-10, cicloalquilalquilo C4-16, arilo C6-10, arilalquilo C7-16, heteroarilo de 5-12 miembros, heteroarilalquilo de 6-18 miembros, heterocicloalquilo de 3-14 miembros y heterocicloalquilalquilo de 4-14 miembros; cada Rf es un sustituyente apropiado y en cada caso de modo independiente entre si está seleccionado del grupo compuesto por -ORg, -SRg, -NRgRg, -ONRgRg, -N(ORg)Rg, -N(Rh)NRgRg, halogeno, -CN, -NC, -OCN, -SCN, -NO, -NO2, -N3, -C(O)Rg, -C(O)OR9, -C(O)NRgRg, -C(O)SRg, -C(O)NRhNRgRg, -C(O)NRhORg, -[C(O)]2NRgRg, -[C(O)NRh]2Rg, -C(S)Rg, -C(S)ORg, -C(S)NRgRg, -C(S)SRg, -C(NRh)Rg, -N=CRgRg, -C(NRh)ORg, -C(NRh)NRgRg, -C(NRh)SRg, -C(NRh)NRhNRgRg, -C(NORh)Rg, -C(NORh)NRgRg, -C(NNRhRh)Rg, -C[NNRhC(O)NRhRh]Rg, -OS(O)Rg, -OS(O)ORg, -OS(O)NRgRg, -OS(O)2Rg, -OS(O)2ORg, OS(O)2NRgRg, -OC(O)Rg, -OC(O)ORg, -OC(O)SRg, -OC(O)NRgRg, -O[C(O)]2NRgRg, -O[CAppropriate for the treatment of diseases that are characterized by excessive or abnormal cell proliferation, as well as their use for the preparation of a drug with the aforementioned properties. Claim 1: Compounds characterized in that they have the general formula (1) wherein R 1 represents a 5-10 membered heteroaryl, optionally substituted with one or more identical or different radicals, in each case, independently of each other, selected from the compound group by Ra and Rb; R2 presents substructure (2) or (3); R3 is selected from the group consisting of hydrogen, halogen, -CN, -NO2, -NRRh, -ORh, -C (O) Rh, -C (O) NRhRh, -SRh, -S (O) Rh, -S ( O) 2Rh, C1-4 alkyl, C1-4 haloalkyl, C3-7 cycloalkyl and 3-7 membered heterocycloalkyl; R 5 is selected from the group consisting of C 1-6 alkyl, -C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 haloalkyl, C 3-7 cycloalkyl, 3-7 membered heterocycloalkyl, all previously mentioned radicals optionally substituted by alkyl C1, -CN or -OH; a) in the presence of the substructure (2) one of the radicals R6, R7 or R8 and b) in the presence of the substructure (3) one of the radicals R6 or R7 presents one of the substructures (4) to (7) and in case a) the two radicals remaining in each case independently of each other and in case b) the second radical is / are selected from the group consisting of hydrogen, C1-6 alkyl, -C1-6 alkyl, -OH, - CN, -N C1-6alkyl, -N (C1-6 alkyl) 2 and halogen oc) in the presence of substructure (i) R5 represents a C1-6 alkyl or C3-4 cycloalkyl substituted with a substituent -CN and R6, R7 and R8 represent hydrogen in each case; R9 is selected from the group consisting of hydrogen and C1-6alkyl, R10 is selected from the group consisting of Ra and -ORa, or the group -NR9R10 generally represents a 3-14 membered heterocycloalkyl containing 5-6 nitrogen or heteroaryl content 12 members, possibly substituted with one or several same or different radicals selected from the group consisting of Ra and Rb; R11, R12 and R13 in each case independently correspond to each other to a Ra radical, or R11 is equivalent to a Ra radical and the NR12R13 group together represents a 3-14 membered heterocycloalkyl with nitrogen content, optionally substituted with one or more same or different radicals selected from the group consisting of Ra and Rb, or R11 and R12 together with the atoms to which they are attached, form a 4-14 membered heterocycloalkyl with nitrogen content, optionally substituted with one or several same or different radicals selected from the group consisting of Ra and Rb, and R13 is equivalent to a radical Ra; R14, R15 and R16 in each case independently of each other are equivalent to a radical Ra, or R14 is equivalent to a radical Ra and the group NR15R16 together represents a 3-14 membered heterocycloalkyl with nitrogen content, optionally substituted with one or more same or different radicals selected from the group consisting of R and Rb, or R14 and R15 together with the atoms to which they are attached, form a 4-14 membered heterocycloalkyl with nitrogen content, optionally substituted with one or several same or different radicals selected from the group consisting of Ra and Rb, and R16 is equivalent to a radical Ra; R17, R18 and R19 in each case independently of each other are equivalent to a radical Ra, or R17 and R18 together with the atoms to which they are attached, form a 3-14 membered heterocycloalkyl with nitrogen content, eventually substituted with one or several identical or different radicals selected from the group consisting of Ra and Rb, and R19 is equivalent to a radical Ra; or R17 and R18 together with the atoms to which they are attached, form a 414-membered nitrogen-containing heterocycloalkyl, optionally substituted with one or more identical or different radicals selected from the group consisting of Ra and Rb, and equivalent to a radical Ra ; or R17 and R18 together with the atoms to which they are attached, form a 414-membered nitrogen-containing heterocycloalkyl, optionally substituted with one or more identical or different radicals selected from the group consisting of Ra and Rb, and R19 equals a radical Ra; L is selected from the group consisting of -C (O) NH-, -NHC (O) -, -C (S) NH-, -NHC (S) -, -C (O) -, -C (S) - , -NH-, -S (O) -, -S (O) O-, -S (O) 2-, -S (O) 2O-, -S (O) NH-, -S (O) 2NH -, -OS (O) -, -OS (O) 2-, -OS (O) NH, -OS (O) 2NH-, -C (O) O-, -C (O) S-, -C (NH) NH-, -OC (O) -, -OC (O) O-, -OC (O) NH-, -SC (O) -, -SC (O) O-, -SC (O) NH -, -NHC (NH) -, -NHS (O) -, -NHS (O) O-, -NHS (O) 2-, -NHS (O) 2O-, -NHS (O) 2NH-, -NHC (O) O-, -NHC (O) NH- and -NHC (S) NH- or represents a bond; Y is selected from the group consisting of -O- and -S- or represents a bond; x e y in each case independently of each other have the value 0, 1, 2 or 3; each Ra is, in each case independently of each other, hydrogen or a radical optionally substituted with one or more, same or different Rb and / or Rc, selected from the group consisting of C1-6 alkyl, 2-6 membered heteroalkyl, C1-6 halogenalkyl, C3-10 cycloalkyl, C4-16 cycloalkylalkyl, C6-10 aryl, C7-16 alkyl aryl, 5-12 membered heteroaryl, 6-18 membered heteroarylalkyl, 3-14 membered heterocycloalkyl and heterocycloalkylalkyl of 4-14 members; each Rb is an appropriate substituent and in each case independently of each other is selected from the group consisting of -ORc, -SRc, -NRcRc, -ONRcRc, -N (ORc) Rc, -NRgNRcRc, halogen, -CN, -NC , -OCN, -SCN, -NO, -NO2, -N3, -C (O) Rc, -C (O) ORc, -C (O) NRcRc, -C (O) SRc, -C (O) NRgNRcRc , -C (O) NRgORc, - [C (O)] 2NRcRc, - [C (O) NRg] 2Rc, -C (S) Rc, -C (S) ORc, -C (S) NRCRC, -C (S) SRc, -C (NRg) Rc, -N = CRcRc, -C (NR9) ORc, -C (NRg) NRc) Rc, -C (NRg) SRc, -C (NRg) NRgNRcRc, -C ( NORg) Rc, -C (NORg) NRcRc, -C (NNRgRg) Rc, -C [NNRgC (O) NRgRg] Rc, -OS (O) Rc, -OS (O) ORc, -OS (O) NRcRc, -OS (O) 2Rc, -OS (O) 2ORc, -OS (O) 2NRcRc, -OC (O) Rc, -OC (O) ORc, -OC (O) SRc, -OC (O) NRcRc, - O [C (O)] 2NRcRc, -O [C (O) NRg] 2NRcRc, -OC (S) Rc, -OC (NRg) Rc, -OC (NRg) NRcRc, -ONRgC (O) Rc, -S (O) Rc, -S (O) ORc, -S (O) NRcRc, -S (O) 2Rc, -S (O) 2ORc, -S (O) 2NRcRc, - [S (O) 2] 2NRcRc, -SC (O) Rc, -SC (O) ORc, -SC (O) NRcRc, -SC (S) Rc, -SC (NRg) Rc, -SC (NRg) NRcRc, -NRgC (O) Rc, - NRgC (O) ORc, -NRgC (O) NRcRc, -NRgC (O) SRc, -NRgC (O) NRgNRcRc, -NRgC (S) Rc, -NRgC (S) NRcRc, -NRgC (NRg) Rc, -N = CRcNRcRc, -NRgC (NRg) ORc, -N RgC (NRg) NRcRc, -NRgC (NRg) SRc, -NRgC (NORg) Rc, -NRgS (O) Rc, -NRgS (O) ORc, -NRgS (O) 2Rc, -NRgS (O) 2ORc, -NRgS (O) 2NRcRc, -NRgNRgC (O) Rc, -NRgNRgC (O) NRcRc, -NRgNRgC (NRg) Rc, -NRg [C (O)] 2Rc, -NRg [C (O)] 2ORc, -NRg [C (O)] 2NRcRc, - [NRgC (O)] 2Rc, - [NRgC (O)] 2ORc, -NRg [S (O) 2] 2Rc, -N (ORg) C (O) Rc, -N [C (O) Rc] NRcRc, -N [C (O) Rc] 2, -N [S (O) 2Rc] 2, -N {[C (O)] 2Rc} 2, -N {[C (O) ] 2ORc} 2 and -N {[C (O)] 2NRcRc} 2 as well as the bivalent substituent = O, = S, = NRg, = NORg, = NNRgRg y = NNRgC (O) NRgRg, where these bivalent substituents only they can be substituents in non-aromatic ring systems; each Rc is, independently of one another, hydrogen or a radical optionally substituted with one or more Rd and / or Re, equal or different, selected from the group consisting of C1-6 alkyl, 2-6 membered heteroalkyl, C1- halogenalkyl 6, C3-10 cycloalkyl, C4-16 cycloalkylalkyl, C6-10 aryl, C7-16 arylalkyl, 5-12 membered heteroaryl, 6-18 membered heteroarylalkyl, 3-14 membered heterocycloalkyl and 4-14 membered heterocycloalkylalkyl; each Rd is an appropriate substituent and in each case independently of each other is selected from the group consisting of -ORe, -SRe, -NReRe, -ONReRe, -N (ORe) Re, -N (Rg) NReRe, halogen, - CN, -NC, -OCN, -SCN, -NO, -NO2, -N3, -C (O) Re, -C (O) ORe, -C (O) NReRe, -C (O) SRe, -C (O) NRgNReRe, -C (O) NRgORe, - [C (O)] 2NReRe, - [C (O) NRg] 2Re, -C (S) Re, -C (S) ORe, -C (S) NReRe, -C (S) SRe, -C (NRg) Re, -N = CReRe, -C (NRg) ORe, -C (NRg) NReRe, -C (NRg) SRe, -C (NRg) NRgNReRe, - C (NORg) Re, -C (NORg) NReRe, -C (NNRgRg) Re, -C [NNRgC (O) NRgRg] Re, -OS (O) Re, -OS (O) ORe, -OS (O) NReRe, -OS (O) 2Re, -OS (O) 2ORe, -OS (O) 2NReRe, -OC (O) Re, -OC (O) ORe, -OC (O) SRe, -OC (O) NReRe , -O [C (O)] 2NReRe, -O [C (O) NRg] 2NReRe, -OC (S) Re, -OC (NRg) Re, -OC (NRg) NReRe, -ONRgC (O) Re, -S (O) Re, -S (O) ORe, -S (O) NReRe, -S (O) 2Re, -S (O) 2ORe, -S (O) 2NReRe, - [S (O) 2] 2NReRe, -SC (O) Re, -SC (O) ORe, -SC (O) NReRe, -SC (S) Re, -SC (NRg) Re, -SC (NRg) NReRe, -NRgC (O) Re , -NRgC (O) ORe, -NRgC (O) NReRe, -NRgC (O) SRe, -NRgC (O) NR9NReRe, -NRgC (S) Re, -NRgC (S) NReRe, -NRgC (NRg) Re, -N = CReNReRe, -NRgC (NRg) ORe, -N RgC (NRg) NReRe, -NRgC (NRg) SRe, -NRgC (NORg) Re, -NRgS (O) Re, -NRgS (O) ORe, -NRgS (O) 2Re, -NRgS (O) 2ORe, -NRgS (O) 2NReRe, -NRgNRgC (O) Re, -NRgNRgC (O) NReRe, -NRgNRgC (NRg) Re, -NRg [C (O)] 2Re, -NRg [C (O)] 2ORe, -NRg [C (O)] 2NReRe, - [NRgC (O)] 2Re, [NRgC (O)] 2ORe, -NRg [S (O) 2] 2Re, -N (ORg) C (O) Re, -N [C ( O) Re] NReRe, -N [C (O) Re] 2, -N [S (O) 2Re] 2, -N {[C (O)] 2Re} 2, -N {[C (O)] 2ORe} 2 and -N {[C (O)] 2NReRe} 2, as well as the bivalent substituent = O, = S, = NRg, = NORg, = NNRgRg y = NNRgC (O) NRgRg, where these bivalent substituents only they can be substituents in non-aromatic ring systems; each Re is, independently of one another, hydrogen or a radical optionally substituted with one or more same or different Rf and / or Rg, selected from the group consisting of C1-6 alkyl, 2-6 membered heteroalkyl, C1-6 halogenalkyl , C3-10 cycloalkyl, C4-16 cycloalkylalkyl, C6-10 aryl, C7-16 arylalkyl, 5-12 membered heteroaryl, 6-18 membered heteroarylalkyl, 3-14 membered heterocycloalkyl and 4-14 membered heterocycloalkylalkyl; each Rf is an appropriate substituent and in each case independently of each other is selected from the group consisting of -ORg, -SRg, -NRgRg, -ONRgRg, -N (ORg) Rg, -N (Rh) NRgRg, halogen, - CN, -NC, -OCN, -SCN, -NO, -NO2, -N3, -C (O) Rg, -C (O) OR9, -C (O) NRgRg, -C (O) SRg, -C (O) NRhNRgRg, -C (O) NRhORg, - [C (O)] 2NRgRg, - [C (O) NRh] 2Rg, -C (S) Rg, -C (S) ORg, -C (S) NRgRg, -C (S) SRg, -C (NRh) Rg, -N = CRgRg, -C (NRh) ORg, -C (NRh) NRgRg, -C (NRh) SRg, -C (NRh) NRhNRgRg, - C (NORh) Rg, -C (NORh) NRgRg, -C (NNRhRh) Rg, -C [NNRhC (O) NRhRh] Rg, -OS (O) Rg, -OS (O) ORg, -OS (O) NRgRg, -OS (O) 2Rg, -OS (O) 2ORg, OS (O) 2NRgRg, -OC (O) Rg, -OC (O) ORg, -OC (O) SRg, -OC (O) NRgRg, -O [C (O)] 2NRgRg, -O [C

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